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A kind of multi-responsive polymer nano-carrier with the characteristics of fast crossing the cell membrane and its synthesis method and application

A nano-carrier and responsive technology, which is applied in the field of multi-responsive polymer nano-carriers and their synthesis, can solve problems such as limiting the application of artificially synthesized polymers, and achieve good biocompatibility and strong interaction effects

Inactive Publication Date: 2018-05-15
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The smooth delivery of drug molecules across the membrane to the nucleus is the key to the implementation of tumor therapy. However, the biological barrier function of the cell membrane will prevent many polymer substances from entering the cell, thus largely limiting the possibility of artificially synthesized polymers as drug carriers. and its application in subsequent treatment

Method used

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  • A kind of multi-responsive polymer nano-carrier with the characteristics of fast crossing the cell membrane and its synthesis method and application
  • A kind of multi-responsive polymer nano-carrier with the characteristics of fast crossing the cell membrane and its synthesis method and application
  • A kind of multi-responsive polymer nano-carrier with the characteristics of fast crossing the cell membrane and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Implementation Example 1: Synthesis of Pentafluorophenol Isonitrile Monomer

[0089] Add p-nitrobenzoic acid (1.1eq), pentafluorophenol (1eq), EDCI (1.2eq), and DMAP (0.5eq) into a two-necked flask, use dichloromethane as a solvent, and react at room temperature. After the reaction is followed by TLC, use Wash 3 times with water, 3 times with saturated sodium bicarbonate solution, 3 times with saturated sodium chloride solution, collect the organic phase, add anhydrous sodium sulfate to dry for 3 hours, remove anhydrous sodium sulfate by suction filtration, remove the solvent by rotary evaporation, pass through a silica gel column After purification (eluent: petroleum ether: ethyl acetate = 1:1), the product was collected, the solvent was removed, and vacuum-dried to constant weight. After passing through a silica gel column (DCM:PE=1:1), the product was collected, spin-dried and then vacuum-dried to constant weight to obtain product I, whose structural formula is:

[...

Embodiment 2

[0098]Implementation example 2: Synthesis of benzyl isonitrile with hydrogen peroxide response

[0099] Pentafluorophenol isonitrile (1eq), 4-hydroxymethylphenylboronic acid pinacol ester (1.1eq), DMAP (1.2eq), and anhydrous THF were added to a two-necked flask, vacuum-filled with nitrogen, and repeated 3 times. Under a nitrogen atmosphere, stir the reaction at 30°C, track the reaction by TLC, spin dry, pass through a silica gel column (DCM:PE=9:1), collect the product, spin dry, vacuum dry to constant weight, and store in a freezer. Benzene with hydrogen peroxide response The synthetic route of isonitrile is as image 3 shown.

Embodiment 3

[0100] Embodiment 3: the synthesis of chiral hydrophilic benzene isonitrile monomer

[0101] Add Cbz-alanine, pentaethylene glycol monomethyl ether, EDCI, and DMAP in a molar ratio of 1:1:1.1:0.2 to a two-necked flask, and react overnight at room temperature with dichloromethane as a solvent. After TLC showed that the reaction was complete, wash 3 times with water, 3 times with saturated sodium bicarbonate solution, and 3 times with saturated sodium chloride solution, collect the organic phase, add anhydrous sodium sulfate to dry for 3 h, remove anhydrous sodium sulfate by suction filtration, and spin The solvent was evaporated and purified by silica gel column (eluent: petroleum ether: ethyl acetate = 1:1), the product was collected, the solvent was removed and dried in vacuo. To obtain product IV, the structural formula is:

[0102]

[0103] Product Ⅳ, Pd / C was added to a two-necked flask at a mass ratio of 1:0.1, THF was added, nitrogen was first replaced, and then hydr...

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Abstract

The invention relates to a multi-responsive polymer nanocarrier with a rapid cell penetrating characteristic. The nanocarrier is formed by self-assembling of a multi-responsive amphipathic triblock copolymer, the nanocarrier adopts an onion structure sequentially comprising an acid-responsive PLLA core, cyanine molecules with a near infrared absorption characteristic, a hydrogen-peroxide-responsive PPI (polyphenyl isocyanide) intermediate layer and a left-handed spiral hydrophilic PPI hydrophilic chain from inside to outside sequentially, wherein the structure of the multi-responsive amphipathic triblock copolymer is shown in the general formula in the specification, R1 is a group with stimulation responsiveness, and R2 is a chiral PEG hydrophilic chain; x ranges from 20 to 50, y ranges from 20 to 50, and z ranges from 30 to 80. The multi-responsive polymer nanocarrier can be used for transporting hydrophobic dye molecules and medicine molecules, can rapidly and efficiently penetrate cell membranes, has multiple stimuli-responsiveness, realizes programmable controlled release of medicines and has a chemical-photothermal collaborative treatment characteristic.

Description

technical field [0001] The invention relates to the field of polymer reaction, and relates to a multi-responsive polymer nanocarrier capable of rapidly passing through cell membranes, a synthesis method and application thereof. Background technique [0002] In recent years, with the rapid development of nanotechnology and synthetic chemistry, more and more attention has been paid to the application of nanocarriers in the field of biomedicine; among them, polymer-based nanocarriers are important for biomedical imaging, diagnosis, and drug delivery. Provides new means and ideas. Studies have shown that nanoscale to submicron-scale carriers have strong adsorption and penetration to tissue mucosa, and nanostructures such as polymer-based micelles and vesicles can "enhance penetration and retention (EPR)" in tumor tissues through enhanced penetration and retention (EPR) effects. Passive targeting" to the tumor site. [0003] For biocompatible amphiphilic block copolymers, when ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/91C08G63/08C08G61/02C08G61/04A61K9/51A61K47/34A61K41/00
CPCA61K9/5146A61K41/0052C08G61/02C08G61/04C08G63/08C08G63/912C08G2261/11C08G2261/148C08G2261/332
Inventor 殷俊张志煌陈宇吴云柱韩鑫张健张文明
Owner HEFEI UNIV OF TECH
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